Identification
YMDB IDYMDB11358
NameCL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(11Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionCL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(11Z)) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(11Z)) contains one chain of (9Z-hexadecenoyl) at the C1 position, three chains of (11Z-octadecenoyl) at the C2, C3 and C4 positions. While the theoretical charge of cardiolipins is -2, under normal physiological conditions (pH near 7), the molecule may carry only one negative charge. In prokaryotes such as E. coli, the enzyme known as diphosphatidylglycerol synthase catalyses the transfer of the phosphatidyl moiety of one phosphatidylglycerol to the free 3'-hydroxyl group of another, with the elimination of one molecule of glycerol. In E. coli, which acylates its glycerophospholipids with acyl chains ranging in length from 12 to 18 carbons and possibly containing an unsaturation, or a cyclopropane group more than 100 possible CL molecular species are theoretically possible, 53 of these species having been characterized. E. coli membranes consist of ~5% cardiolipin (CL), 20-25% phosphatidylglycerol (PG), and 70-80% phosphatidylethanolamine (PE) as well as smaller amounts of phosphatidylserine (PS). CL is distributed between the two leaflets of the bilayers and is located preferentially at the poles and septa in E. coli and other rod-shaped bacteria. It is known that the polar positioning of the proline transporter ProP and the mechanosensitive ion channel MscS in E. coli is dependent on CL. It is believed that cell shape may influence the localization of CL and the localization of certain membrane proteins.
Structure
Thumb
Synonyms
  • Cardiolipin(16:1/18:1/18:1/18:1)
  • CL(16:1/18:1/18:1/18:1)
  • CL(70:4)
  • 1'-[1-Palmitoleoyl-2-vaccenoyl-sn-glycero-3-phospho],3'-[1,2-divaccenoyl-rac-glycero-3-phospho]-glycerol
  • CL(1'-[16:1(9Z)/18:1(11Z)],3'-[18:1(11Z)/18:1(11Z)])
  • 1'-[1-(9Z-Hexadecenoyl)-2-(11Z-octadecenoyl)-sn-glycero-3-phospho],3'-[1,2-di(11Z-octadecenoyl)-rac-glycero-3-phospho]-glycerol
  • Cardiolipin(70:4)
  • CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(11Z))
CAS numberNot Available
WeightAverage: 1429.968
Monoisotopic: 1429.003527237
InChI KeyRVFOFBDVSIUZIY-AMGQDKLXSA-N
InChIInChI=1S/C79H146O17P2/c1-5-9-13-17-21-25-29-33-36-40-44-48-52-56-60-64-77(82)90-70-75(96-79(84)66-62-58-54-50-46-42-38-35-31-27-23-19-15-11-7-3)72-94-98(87,88)92-68-73(80)67-91-97(85,86)93-71-74(69-89-76(81)63-59-55-51-47-43-39-32-28-24-20-16-12-8-4)95-78(83)65-61-57-53-49-45-41-37-34-30-26-22-18-14-10-6-2/h25-32,73-75,80H,5-24,33-72H2,1-4H3,(H,85,86)(H,87,88)/b29-25-,30-26-,31-27-,32-28-/t73-,74+,75+/m0/s1
IUPAC Name[(2R)-3-({[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acid
Traditional IUPAC Name(2R)-3-{[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(11Z)-octadec-11-enoyloxy]propoxy)phosphinic acid
Chemical FormulaC79H146O17P2
SMILES[H][C@@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as cardiolipins. These are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,2-diacylglycerol chain. Their general formula is OC(COP(O)(=O)OC[C@@H](CO[R1])O[R2])COP(O)(=O)OC[C@@H](CO[R3])O[R4], where R1-R4 are four fatty acyl chains.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerophosphoglycerols
Direct ParentCardiolipins
Alternative Parents
Substituents
  • Cardiolipin
  • Tetracarboxylic acid or derivatives
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility7.2e-05 g/LALOGPS
logP9.05ALOGPS
logP24.93ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)1.59ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area236.95 ŲChemAxon
Rotatable Bond Count80ChemAxon
Refractivity402.17 m³·mol⁻¹ChemAxon
Polarizability169.1 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Mitochondrion membrane
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0030000900-a5b5a4174639a1cc40b9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0031110900-a268073b38374911334aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uzi-0093300000-e191533ed661ba6ea6f5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02ta-0941511330-f79ff8f58ec24faf5a58JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0972304170-1e5dcb14144d182b01a7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bj-1498423320-e1b04e9930033d525d12JSpectraViewer
References
References:
  • Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB0057566
Pubchem Compound ID131767868
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDFDB032584
Wikipedia IDNot Available
BioCyc IDNot Available